NPASS Compound

Structure

NPC50438 OpenBabel07101718192D 32 35 0 0 1 0 0 0 0 0999 V2000 -4.7515 2.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0387 3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 3.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4593 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4133 3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0605 3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 2.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3914 4.1270 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7004 5.0780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1261 -0.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 17 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 13 21 1 0 0 0 0 14 22 1 0 0 0 0 14 27 1 0 0 0 0 15 20 1 0 0 0 0 16 3 1 1 0 0 0 16 18 1 0 0 0 0 17 28 1 6 0 0 0 18 26 1 6 0 0 0 19 22 1 0 0 0 0 19 25 1 6 0 0 0 20 29 1 1 0 0 0 21 24 1 0 0 0 0 21 30 2 0 0 0 0 22 31 1 1 0 0 0 23 25 1 6 0 0 0 23 27 1 0 0 0 0 24 26 1 6 0 0 0 24 27 1 0 0 0 0 25 4 1 6 0 0 0 26 5 1 6 0 0 0 27 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	450.33
Volume:	482.637
LogP:	3.65
LogD:	3.877
LogS:	-3.967
# Rotatable Bonds:	5
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	5.091
Fsp3:	0.963
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.833
MDCK Permeability:	1.0335495971958153e-05
Pgp-inhibitor:	0.3
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.727
30% Bioavailability (F30%):	0.309

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.298
Plasma Protein Binding (PPB):	82.0383071899414%
Volume Distribution (VD):	0.915
Pgp-substrate:	9.738940238952637%

ADMET: Metabolism

CYP1A2-inhibitor:	0.008
CYP1A2-substrate:	0.75
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.798
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.001
CYP2D6-substrate:	0.097
CYP3A4-inhibitor:	0.361
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	11.811
Half-life (T1/2):	0.213

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.402
Drug-inuced Liver Injury (DILI):	0.038
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.257
Maximum Recommended Daily Dose:	0.767
Skin Sensitization:	0.316
Carcinogencity:	0.125
Eye Corrosion:	0.162
Eye Irritation:	0.038
Respiratory Toxicity:	0.98

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC50438

Natural Product ID:	NPC50438
*Common Name:**	Certonardosterol Q3
IUPAC Name:	(3S,5S,6S,8S,9R,10S,13R,14R,17R)-3,6,8-trihydroxy-17-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,5,6,7,9,11,12,14,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-15-one
Synonyms:	Certonardosterol Q3
Standard InCHIKey:	HRUJIYHHMYANHN-RLSMRNFZSA-N
Standard InCHI:	InChI=1S/C27H46O5/c1-15(2)20(29)7-6-16(3)18-13-21(30)24-26(18,5)11-9-23-25(4)10-8-17(28)12-19(25)22(31)14-27(23,24)32/h15-20,22-24,28-29,31-32H,6-14H2,1-5H3/t16-,17+,18-,19-,20+,22+,23-,24-,25+,26-,27+/m1/s1
SMILES:	CC(C)[C@H](CC[C@@H](C)[C@H]1CC(=O)[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H](C[C@@H]3[C@H](C[C@@]21O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456308
PubChem CID:	21589762
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0001104] Trihydroxy bile acids, alcohols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12444692]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662097]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104487]
NPO7293	Certonardoa semiregularis	Species	Ophidiasteridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497935]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	13.6	ug ml-1	PMID[478630]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	12.6	ug ml-1	PMID[478630]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	5.43	ug ml-1	PMID[478630]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	12.3	ug ml-1	PMID[478630]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	7.3	ug ml-1	PMID[478630]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC50438 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	3301
0.2-0.3	8962
0.3-0.4	14161
0.4-0.5	6056
0.5-0.6	5277
0.6-0.7	3408
0.7-0.8	936
0.8-0.85	162
0.85-0.9	49
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC263802
0.9167	High Similarity	NPC61688
0.9048	High Similarity	NPC226491
0.9048	High Similarity	NPC477614
0.9036	High Similarity	NPC302111
0.8941	High Similarity	NPC24705
0.8941	High Similarity	NPC56962
0.8902	High Similarity	NPC327451
0.8846	High Similarity	NPC159789
0.8837	High Similarity	NPC476296
0.881	High Similarity	NPC476727
0.881	High Similarity	NPC476726
0.878	High Similarity	NPC268040
0.8734	High Similarity	NPC472487
0.8734	High Similarity	NPC472486
0.8667	High Similarity	NPC170978
0.8659	High Similarity	NPC254123
0.8659	High Similarity	NPC469745
0.8652	High Similarity	NPC62407
0.8652	High Similarity	NPC287354
0.8642	High Similarity	NPC320144
0.8636	High Similarity	NPC476189
0.8625	High Similarity	NPC221420
0.8625	High Similarity	NPC475031
0.8608	High Similarity	NPC21220
0.8608	High Similarity	NPC125767
0.859	High Similarity	NPC232112
0.8588	High Similarity	NPC472272
0.8588	High Similarity	NPC80700
0.8571	High Similarity	NPC471044
0.8571	High Similarity	NPC473336
0.8554	High Similarity	NPC317066
0.8519	High Similarity	NPC34046
0.8519	High Similarity	NPC324700
0.8519	High Similarity	NPC224802
0.8519	High Similarity	NPC80089
0.8519	High Similarity	NPC171426
0.8519	High Similarity	NPC185465
0.85	High Similarity	NPC475742
0.85	High Similarity	NPC5767
0.8488	Intermediate Similarity	NPC202937
0.8471	Intermediate Similarity	NPC473350
0.8462	Intermediate Similarity	NPC58057
0.8462	Intermediate Similarity	NPC320549
0.8462	Intermediate Similarity	NPC156277
0.8462	Intermediate Similarity	NPC151018
0.8444	Intermediate Similarity	NPC17336
0.8415	Intermediate Similarity	NPC80891
0.8415	Intermediate Similarity	NPC201276
0.8395	Intermediate Similarity	NPC23884
0.8395	Intermediate Similarity	NPC207010
0.8395	Intermediate Similarity	NPC317913
0.8375	Intermediate Similarity	NPC97534
0.8375	Intermediate Similarity	NPC174964
0.8375	Intermediate Similarity	NPC195155
0.8375	Intermediate Similarity	NPC273366
0.8372	Intermediate Similarity	NPC83242
0.837	Intermediate Similarity	NPC476294
0.8353	Intermediate Similarity	NPC477434
0.8333	Intermediate Similarity	NPC121121
0.8313	Intermediate Similarity	NPC477851
0.8313	Intermediate Similarity	NPC470609
0.8272	Intermediate Similarity	NPC4209
0.8261	Intermediate Similarity	NPC111187
0.8261	Intermediate Similarity	NPC190080
0.825	Intermediate Similarity	NPC133922
0.825	Intermediate Similarity	NPC254340
0.825	Intermediate Similarity	NPC304499
0.8242	Intermediate Similarity	NPC263135
0.8242	Intermediate Similarity	NPC288906
0.8235	Intermediate Similarity	NPC268578
0.8235	Intermediate Similarity	NPC217559
0.8235	Intermediate Similarity	NPC292458
0.8228	Intermediate Similarity	NPC89310
0.8205	Intermediate Similarity	NPC213178
0.8205	Intermediate Similarity	NPC66407
0.8205	Intermediate Similarity	NPC6120
0.8205	Intermediate Similarity	NPC131892
0.8205	Intermediate Similarity	NPC327728
0.8202	Intermediate Similarity	NPC46758
0.8171	Intermediate Similarity	NPC264602
0.8152	Intermediate Similarity	NPC116683
0.8148	Intermediate Similarity	NPC243027
0.8148	Intermediate Similarity	NPC196136
0.8148	Intermediate Similarity	NPC212733
0.8148	Intermediate Similarity	NPC158208
0.814	Intermediate Similarity	NPC25037
0.814	Intermediate Similarity	NPC219535
0.814	Intermediate Similarity	NPC34984
0.814	Intermediate Similarity	NPC237938
0.814	Intermediate Similarity	NPC319909
0.8132	Intermediate Similarity	NPC29247
0.8132	Intermediate Similarity	NPC129004
0.8132	Intermediate Similarity	NPC101233
0.8132	Intermediate Similarity	NPC289539
0.8132	Intermediate Similarity	NPC153775
0.8132	Intermediate Similarity	NPC111524
0.8132	Intermediate Similarity	NPC91772
0.8132	Intermediate Similarity	NPC261333
0.8132	Intermediate Similarity	NPC292374
0.8132	Intermediate Similarity	NPC215271
0.8132	Intermediate Similarity	NPC104371
0.8118	Intermediate Similarity	NPC328007
0.8118	Intermediate Similarity	NPC61107
0.8118	Intermediate Similarity	NPC30583
0.8118	Intermediate Similarity	NPC289486
0.8111	Intermediate Similarity	NPC52756
0.809	Intermediate Similarity	NPC200580
0.809	Intermediate Similarity	NPC471459
0.809	Intermediate Similarity	NPC477443
0.809	Intermediate Similarity	NPC67653
0.809	Intermediate Similarity	NPC477440
0.8068	Intermediate Similarity	NPC57469
0.8068	Intermediate Similarity	NPC259009
0.8046	Intermediate Similarity	NPC477205
0.8043	Intermediate Similarity	NPC231060
0.8043	Intermediate Similarity	NPC138245
0.8043	Intermediate Similarity	NPC84018
0.8025	Intermediate Similarity	NPC192501
0.8025	Intermediate Similarity	NPC167702
0.8025	Intermediate Similarity	NPC10476
0.8025	Intermediate Similarity	NPC477930
0.8025	Intermediate Similarity	NPC228994
0.8025	Intermediate Similarity	NPC280026
0.8022	Intermediate Similarity	NPC144739
0.8022	Intermediate Similarity	NPC181594
0.8	Intermediate Similarity	NPC475056
0.8	Intermediate Similarity	NPC473267
0.8	Intermediate Similarity	NPC477433
0.8	Intermediate Similarity	NPC46848
0.8	Intermediate Similarity	NPC470071
0.8	Intermediate Similarity	NPC71706
0.8	Intermediate Similarity	NPC252182
0.8	Intermediate Similarity	NPC12933
0.8	Intermediate Similarity	NPC77756
0.8	Intermediate Similarity	NPC477444
0.8	Intermediate Similarity	NPC1340
0.8	Intermediate Similarity	NPC476071
0.8	Intermediate Similarity	NPC187471
0.8	Intermediate Similarity	NPC127094
0.8	Intermediate Similarity	NPC477442
0.8	Intermediate Similarity	NPC80401
0.7978	Intermediate Similarity	NPC90676
0.7976	Intermediate Similarity	NPC52951
0.7957	Intermediate Similarity	NPC234564
0.7957	Intermediate Similarity	NPC476728
0.7957	Intermediate Similarity	NPC264979
0.7957	Intermediate Similarity	NPC193785
0.7957	Intermediate Similarity	NPC135548
0.7955	Intermediate Similarity	NPC472745
0.7952	Intermediate Similarity	NPC185915
0.7952	Intermediate Similarity	NPC105208
0.7952	Intermediate Similarity	NPC192046
0.7952	Intermediate Similarity	NPC477918
0.7952	Intermediate Similarity	NPC477227
0.7952	Intermediate Similarity	NPC143133
0.7952	Intermediate Similarity	NPC298168
0.7952	Intermediate Similarity	NPC128951
0.7952	Intermediate Similarity	NPC302578
0.7949	Intermediate Similarity	NPC472984
0.7935	Intermediate Similarity	NPC302008
0.7935	Intermediate Similarity	NPC191094
0.7931	Intermediate Similarity	NPC475689
0.7927	Intermediate Similarity	NPC35871
0.7927	Intermediate Similarity	NPC317242
0.7927	Intermediate Similarity	NPC68565
0.7917	Intermediate Similarity	NPC471254
0.7917	Intermediate Similarity	NPC275990
0.7912	Intermediate Similarity	NPC299185
0.7912	Intermediate Similarity	NPC198242
0.7912	Intermediate Similarity	NPC211403
0.7912	Intermediate Similarity	NPC476168
0.7907	Intermediate Similarity	NPC154043
0.7907	Intermediate Similarity	NPC60018
0.7907	Intermediate Similarity	NPC202688
0.7901	Intermediate Similarity	NPC310766
0.7895	Intermediate Similarity	NPC41971
0.7895	Intermediate Similarity	NPC37047
0.7895	Intermediate Similarity	NPC180733
0.7895	Intermediate Similarity	NPC127408
0.7895	Intermediate Similarity	NPC94906
0.7895	Intermediate Similarity	NPC291785
0.7875	Intermediate Similarity	NPC63588
0.7875	Intermediate Similarity	NPC192192
0.7875	Intermediate Similarity	NPC476731
0.7875	Intermediate Similarity	NPC232925
0.7875	Intermediate Similarity	NPC251201
0.7872	Intermediate Similarity	NPC253586
0.7865	Intermediate Similarity	NPC153604
0.7865	Intermediate Similarity	NPC252714
0.7857	Intermediate Similarity	NPC67657
0.7857	Intermediate Similarity	NPC147993
0.7857	Intermediate Similarity	NPC475725
0.7857	Intermediate Similarity	NPC18857
0.7849	Intermediate Similarity	NPC266431
0.7849	Intermediate Similarity	NPC305808
0.7841	Intermediate Similarity	NPC471034
0.7841	Intermediate Similarity	NPC131350
0.7841	Intermediate Similarity	NPC190704
0.7835	Intermediate Similarity	NPC34562

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC50438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	3614
0.2-0.3	3436
0.3-0.4	1036
0.4-0.5	261
0.5-0.6	208
0.6-0.7	146
0.7-0.8	31
0.8-0.85	7
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8846	High Similarity	NPD3703	Phase 2
0.8519	High Similarity	NPD6115	Approved
0.8519	High Similarity	NPD6118	Approved
0.8519	High Similarity	NPD6114	Approved
0.8519	High Similarity	NPD6697	Approved
0.8462	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD6116	Phase 1
0.8272	Intermediate Similarity	NPD6117	Approved
0.8205	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD5360	Phase 3
0.8077	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD4789	Approved
0.7875	Intermediate Similarity	NPD4244	Approved
0.7875	Intermediate Similarity	NPD4245	Approved
0.775	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3698	Phase 2
0.7692	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4758	Discontinued
0.7442	Intermediate Similarity	NPD3671	Phase 1
0.7442	Intermediate Similarity	NPD5364	Discontinued
0.7349	Intermediate Similarity	NPD6081	Approved
0.732	Intermediate Similarity	NPD4755	Approved
0.7312	Intermediate Similarity	NPD5328	Approved
0.7253	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD4634	Approved
0.7172	Intermediate Similarity	NPD4700	Approved
0.7172	Intermediate Similarity	NPD5286	Approved
0.7172	Intermediate Similarity	NPD4696	Approved
0.7172	Intermediate Similarity	NPD5285	Approved
0.716	Intermediate Similarity	NPD4224	Phase 2
0.7158	Intermediate Similarity	NPD6079	Approved
0.7093	Intermediate Similarity	NPD3702	Approved
0.7033	Intermediate Similarity	NPD4788	Approved
0.703	Intermediate Similarity	NPD4633	Approved
0.703	Intermediate Similarity	NPD5226	Approved
0.703	Intermediate Similarity	NPD5211	Phase 2
0.703	Intermediate Similarity	NPD5224	Approved
0.703	Intermediate Similarity	NPD5225	Approved
0.7024	Intermediate Similarity	NPD4787	Phase 1
0.7019	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7128	Approved
0.699	Remote Similarity	NPD6402	Approved
0.699	Remote Similarity	NPD6675	Approved
0.699	Remote Similarity	NPD5739	Approved
0.6979	Remote Similarity	NPD8034	Phase 2
0.6979	Remote Similarity	NPD8035	Phase 2
0.6961	Remote Similarity	NPD5175	Approved
0.6961	Remote Similarity	NPD5174	Approved
0.6957	Remote Similarity	NPD4786	Approved
0.6941	Remote Similarity	NPD5777	Approved
0.6931	Remote Similarity	NPD1700	Approved
0.6931	Remote Similarity	NPD5223	Approved
0.6907	Remote Similarity	NPD4202	Approved
0.6893	Remote Similarity	NPD5141	Approved
0.6889	Remote Similarity	NPD7525	Registered
0.6869	Remote Similarity	NPD5221	Approved
0.6869	Remote Similarity	NPD5222	Approved
0.6869	Remote Similarity	NPD4697	Phase 3
0.6869	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6881	Approved
0.6857	Remote Similarity	NPD6899	Approved
0.6857	Remote Similarity	NPD7320	Approved
0.6832	Remote Similarity	NPD8418	Phase 2
0.6827	Remote Similarity	NPD4768	Approved
0.6827	Remote Similarity	NPD4767	Approved
0.6809	Remote Similarity	NPD3618	Phase 1
0.68	Remote Similarity	NPD5173	Approved
0.6796	Remote Similarity	NPD4754	Approved
0.6792	Remote Similarity	NPD6373	Approved
0.6792	Remote Similarity	NPD6372	Approved
0.6786	Remote Similarity	NPD6054	Approved
0.6786	Remote Similarity	NPD6059	Approved
0.6762	Remote Similarity	NPD5697	Approved
0.6762	Remote Similarity	NPD5701	Approved
0.6739	Remote Similarity	NPD3667	Approved
0.6729	Remote Similarity	NPD7290	Approved
0.6729	Remote Similarity	NPD6883	Approved
0.6729	Remote Similarity	NPD7102	Approved
0.6703	Remote Similarity	NPD6928	Phase 2
0.6698	Remote Similarity	NPD4730	Approved
0.6698	Remote Similarity	NPD4729	Approved
0.6698	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6637	Remote Similarity	NPD6319	Approved
0.6636	Remote Similarity	NPD6013	Approved
0.6636	Remote Similarity	NPD6012	Approved
0.6636	Remote Similarity	NPD6014	Approved
0.6632	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD8297	Approved
0.6606	Remote Similarity	NPD6882	Approved
0.6598	Remote Similarity	NPD4753	Phase 2
0.6579	Remote Similarity	NPD6016	Approved
0.6579	Remote Similarity	NPD6015	Approved
0.6574	Remote Similarity	NPD5250	Approved
0.6574	Remote Similarity	NPD5251	Approved
0.6574	Remote Similarity	NPD5248	Approved
0.6574	Remote Similarity	NPD5247	Approved
0.6574	Remote Similarity	NPD5249	Phase 3
0.6566	Remote Similarity	NPD6399	Phase 3
0.6552	Remote Similarity	NPD7492	Approved
0.6545	Remote Similarity	NPD4632	Approved
0.6542	Remote Similarity	NPD6011	Approved
0.6525	Remote Similarity	NPD7736	Approved
0.6522	Remote Similarity	NPD5988	Approved
0.6514	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5216	Approved
0.6514	Remote Similarity	NPD5217	Approved
0.6514	Remote Similarity	NPD5215	Approved
0.6496	Remote Similarity	NPD6616	Approved
0.6471	Remote Similarity	NPD7319	Approved
0.6465	Remote Similarity	NPD7515	Phase 2
0.6441	Remote Similarity	NPD7078	Approved
0.6441	Remote Similarity	NPD8293	Discontinued
0.6422	Remote Similarity	NPD5135	Approved
0.6422	Remote Similarity	NPD5169	Approved
0.6422	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD3133	Approved
0.6421	Remote Similarity	NPD3666	Approved
0.6421	Remote Similarity	NPD3665	Phase 1
0.6408	Remote Similarity	NPD7638	Approved
0.6372	Remote Similarity	NPD6009	Approved
0.6364	Remote Similarity	NPD5127	Approved
0.6355	Remote Similarity	NPD6008	Approved
0.6355	Remote Similarity	NPD6920	Discontinued
0.6346	Remote Similarity	NPD7639	Approved
0.6346	Remote Similarity	NPD7640	Approved
0.6311	Remote Similarity	NPD6084	Phase 2
0.6311	Remote Similarity	NPD6083	Phase 2
0.6293	Remote Similarity	NPD6921	Approved
0.6283	Remote Similarity	NPD6274	Approved
0.6275	Remote Similarity	NPD4629	Approved
0.6275	Remote Similarity	NPD5210	Approved
0.6261	Remote Similarity	NPD7100	Approved
0.6261	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD6033	Approved
0.625	Remote Similarity	NPD3668	Phase 3
0.625	Remote Similarity	NPD8133	Approved
0.6239	Remote Similarity	NPD5168	Approved
0.6238	Remote Similarity	NPD8171	Discontinued
0.6228	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD7115	Discovery
0.6226	Remote Similarity	NPD7632	Discontinued
0.6218	Remote Similarity	NPD7507	Approved
0.6211	Remote Similarity	NPD4221	Approved
0.6211	Remote Similarity	NPD4223	Phase 3
0.62	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6700	Approved
0.6195	Remote Similarity	NPD5167	Approved
0.6186	Remote Similarity	NPD5329	Approved
0.6186	Remote Similarity	NPD7604	Phase 2
0.6182	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7748	Approved
0.6174	Remote Similarity	NPD6335	Approved
0.6154	Remote Similarity	NPD7902	Approved
0.6154	Remote Similarity	NPD6909	Approved
0.6154	Remote Similarity	NPD5983	Phase 2
0.6154	Remote Similarity	NPD6908	Approved
0.6147	Remote Similarity	NPD6412	Phase 2
0.614	Remote Similarity	NPD6940	Discontinued
0.6139	Remote Similarity	NPD6703	Approved
0.6139	Remote Similarity	NPD6702	Approved
0.6129	Remote Similarity	NPD3617	Approved
0.6129	Remote Similarity	NPD4238	Approved
0.6129	Remote Similarity	NPD4802	Phase 2
0.6122	Remote Similarity	NPD5279	Phase 3
0.6118	Remote Similarity	NPD371	Approved
0.6106	Remote Similarity	NPD8298	Phase 2
0.6105	Remote Similarity	NPD4692	Approved
0.6105	Remote Similarity	NPD4139	Approved
0.6087	Remote Similarity	NPD6317	Approved
0.6083	Remote Similarity	NPD6336	Discontinued
0.6082	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD4197	Approved
0.605	Remote Similarity	NPD8328	Phase 3
0.6036	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6314	Approved
0.6034	Remote Similarity	NPD6313	Approved
0.6024	Remote Similarity	NPD3198	Approved
0.6	Remote Similarity	NPD6868	Approved
0.6	Remote Similarity	NPD6930	Phase 2
0.6	Remote Similarity	NPD6931	Approved
0.5983	Remote Similarity	NPD4522	Approved
0.5982	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7637	Suspended
0.598	Remote Similarity	NPD6411	Approved
0.5979	Remote Similarity	NPD6695	Phase 3
0.5978	Remote Similarity	NPD6942	Approved
0.5978	Remote Similarity	NPD7339	Approved
0.5962	Remote Similarity	NPD5695	Phase 3
0.596	Remote Similarity	NPD4690	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data